Airbnb Founder: The Number 1 Thing People Get Wrong About Happiness and Success | Brian Chesky

Added: Sep 18, 2023

Chesky begins by reflecting on what makes him happy today and how it differs from what made him happy 16 years ago. He explains that when he first started Airbnb, his motivation was to climb the mountain of success and achieve financial and professional goals. However, as he reached the top of the mountain and achieved success, he realized that true happiness comes from doing what he loves and working with people he cares about. He emphasizes the importance of surrounding oneself with people who share the same values and have complementary skills.

The conversation then shifts to the challenges of building something with friends and maintaining strong relationships as the company grows. Chesky acknowledges that success can amplify both positive and negative aspects of one's personality, and it is important to have a strong foundation of friendship and mutual respect to navigate these challenges. He shares that the key to maintaining a strong bond with his co-founders was their commitment to never let any decision supersede their friendship.

Loneliness is a topic that Chesky delves into, highlighting the loneliness he experienced as he transitioned from a founder to a CEO. He explains that success can be isolating, and he was not prepared for the loneliness that came with it. He shares his realization that loneliness is a prevalent issue in society, with studies showing that chronic loneliness can be worse for one's health than smoking a pack of cigarettes a day. Chesky emphasizes the importance of maintaining deep connections and relationships, as they provide grounding and support in times of isolation.

Chesky discusses his personal journey with loneliness and the steps he took to address it. He shares that he rekindled relationships with old friends, committed to spending more time with loved ones, and even got a dog to bring more joy and connection into his life. He also mentions the influence of former President Barack Obama, who became a mentor to him and emphasized the importance of deep connections and relationships in staying grounded.

The conversation then turns to the concept of loneliness on a broader scale. Chesky discusses how modern life, with its increasing digitization and reliance on technology, can contribute to feelings of loneliness and disconnection. He expresses his concern about the future and the need to design a society that prioritizes human connection and relationships.

Chesky continues by sharing his vision for Airbnb as a community that fosters connection and helps combat loneliness. He believes that travel can be a powerful tool for building relationships and connecting with others. He sees Airbnb's role as not just a travel service but as a platform for creating trust and facilitating meaningful connections between people.

Chesky goes on to emphasize the importance of pursuing one's passion and finding fulfillment in the work they do. He believes that true success comes from designing something amazing and making a positive impact, rather than solely focusing on making money. He highlights the need for a balance between the head and the heart in business, as many companies lose their creative spirit as they grow.

He also discusses the importance of diversity in corporate America, particularly the need for a diversity of artists and scientists. Chesky believes that creativity and imagination are essential for solving the world's biggest problems, and that companies should strive to have a balance of both artistic and analytical minds in their leadership teams.

Chesky reflects on his own journey and the various experiences that have shaped him. He emphasizes the value of curiosity, intuition, and following one's interests and passions. He believes that accumulating diverse experiences and knowledge is crucial for creativity and innovation.

He also discusses the concept of solitude and the importance of being comfortable with oneself. Chesky shares his experience of living as a monk and how it taught him the value of solitude and self-reflection. He believes that true creativity and self-discovery come from exploring the darkest parts of oneself and embracing curiosity.

Chesky draws inspiration from Steve Jobs and his advice to Mark Zuckerberg to go live in an ashram in India to find direction for Facebook. He believes that connecting with oneself and exploring one's inner thoughts and feelings is essential for personal growth and clarity.

He also discusses the concept of being misunderstood and the importance of being willing to be misunderstood in order to bring about revolutionary ideas and change. Chesky believes that true creativity comes from connecting the dots where others see anomalies and being willing to challenge the status quo.

Chesky reflects on his own personal journey and the challenges he faces. He admits that he often worries about what others think of him and seeks validation from others. He also expresses a desire to find clarity and happiness in his personal life, as he feels that he has achieved success professionally but still has unanswered questions about his personal fulfillment.

He acknowledges that his clarity and focus in his professional life have not translated to his personal life, and he is still searching for answers. Chesky believes that having curiosity, role models, and taking action are key to finding clarity and fulfillment in life.

Chesky also discusses the challenges of running a large company and the pressure to maintain its original vision and values. He shares his experience of rebuilding Airbnb from the ground up during the COVID-19 pandemic and the lessons he learned about the importance of maintaining a sense of community and creativity within the company.

Chesky continues by discussing how he thinks in terms of language and numbers, which is influenced by his background. He reflects on the process of designing a world that others want to live in and how he sometimes vicariously lives through the experiences of others. However, he also acknowledges the importance of stepping inside that world himself and living it fully.

He mentions that many tech founders design the world they want to live in because they were dissatisfied with the world they grew up in. However, he emphasizes the need for these leaders to actually live in that world themselves and not lose sight of their own desires and values.

Chesky shares his own experiences of getting disconnected from himself and his purpose as he became more focused on the success of Airbnb. He talks about the pressure from shareholders, employees, and other stakeholders, and how it can be easy to forget why you started in the first place. He emphasizes the importance of reconnecting with oneself and finding one's way back home.

He reflects on his personal life and describes himself as a childlike person with curiosity, energy, and love. He sees the world through the lens of family and community, and he strives to redefine the concept of family and create a sense of connection and belonging.

Chesky discusses the tension between scale and personal significance. He talks about how as a founder, he has to constantly zoom in and zoom out, seeing the big picture while also paying attention to the smallest details. He believes that everything in the universe is connected, but that doesn't mean everything is the same. He emphasizes the importance of finding connections and relationships, both in business and in personal relationships.

He talks about the power of curiosity and fascination, and how they can help us connect with others and discover the beauty and uniqueness in everything. He believes that everything is interdependent and that recognizing our interconnectedness can lead to a greater sense of fulfillment and happiness.

Chesky shares some valuable insights and advice throughout the podcast. He talks about the importance of embracing the paradoxes in life and finding a balance between different aspects of ourselves. He encourages people to be interested in others and to find something fascinating in everything and everyone. He also emphasizes the need for self-reflection and self-discovery, and the importance of living a life aligned with one's values and purpose.

In the final part of the podcast, Chesky shares the best advice he has received, which is to have a hundred people love you rather than a million people just liking you. He also talks about the worst advice he has heard, which is to chase status. He defines his current purpose as trying to bring the world together. When asked how he would like to be remembered, he hopes to be missed. Finally, when asked to create one law that everyone in the world had to follow, he suggests that everyone should live someone else's life and step into someone else's shoes to foster greater understanding and empathy.